5/5 - Excellent
Krista
Aug 12, 2019Chestertown is a beautiful place.
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
The price is ₩110,628 per night from Jun 18 to Jun 19
₩110,628
per night
Jun 18 - Jun 19
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attraction Rolphs Wharf Marina is located nearby.
7.2/10 Good! (277 reviews)
"We have stayed here many times before and I was able to book a one night stay for our quick trip this time. Very comfortable and relaxing, rooms are nice"
Reviewed on May 31, 2024
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
The price is ₩174,888 per night from Jun 20 to Jun 21
₩174,888
per night
Jun 20 - Jun 21
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (679 reviews)
"It was great"
Reviewed on Jun 3, 2024
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
The price is ₩187,023 per night from Jul 3 to Jul 4
₩187,023
per night
Jul 3 - Jul 4
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,628 reviews)
"Love it!"
Reviewed on Jun 5, 2024
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Majestic Hotel & Apartments
7th St & Boardwalk, Ocean City, MD
Stay at this 3-star beach aparthotel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
6.4/10 (74 reviews)
"The rocking chairs facing the ocean."
Reviewed on Jun 3, 2024
WhyHotel by Placemakr Columbia
6200 Valencia Ln, Columbia, MD
Stay at this 4-star aparthotel in Columbia. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (396 reviews)
"Perfect property for families. The apartment had everything you need."
Reviewed on Jun 4, 2024
Shore Point Cottages
9543 Stephen Decatur Hwy, Berlin, MD
Stay at this 3-star cottage in Berlin. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ocean City Beach and Ocean City Boardwalk are ...
9.2/10 Wonderful! (67 reviews)
"It was nice . Will be back"
Reviewed on Jun 5, 2024
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Washington College
4/5(13 reviews)
Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
River Arts Chestertown
Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.
Garfield Center for the Arts at the Prince Theater
You can get tickets for a performance at Garfield Center for the Arts at the Prince Theater on your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Historical Society of Kent County Maryland
You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Wilmer Park
Explore the great outdoors at Wilmer Park, a lovely green space in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Reviews of Chestertown
4.1
Top Destination
5/5 - Excellent
Verified traveler
Jul 24, 2019None of the choices Expedia gave me for places I went to were anywhere near Chestertown. Chestertown is a very nice community with wonderful Colonial Houses, a nice harbour, interesting history, and an amazing number of great restaurants.
4/5 - Good
Verified traveler
Jun 17, 2019Definitely the Land of Pleasant Living!
3/5 - Okay
jana
Jun 13, 2019We went to Washington College. Downtown Chestertown was cute.
4/5 - Good
WashDad23
Apr 19, 2019Small attractive college town on the bay, good restaurants, nice period houses
5/5 - Excellent
Verified traveler
Apr 11, 2019We were in Chestertown to visit Washington College. The town is so special and lovely! I would really love to visit when the weather is warmer to enjoy the water and all the offerings in the area.